Discipline: Chemistry and Chemical Sciences
Subcategory: Plant Research
Kaila Holloway - Howard University
Co-Author(s): Patt Rajitvanit, Chulalongkorn University, Bangkok, Thailand
Miroestrol is a phytoestrogen compound found in the Thai herb Pueraria mirifica that mimics the biological activity of the hormone estrogen. Because of its advantageous properties, the compound is widely used throughout the Thai community as an herbal hormone supplement that is believed to relieve menopausal symptoms and reduce wrinkles (Patisaul & Jefferson 2010). Although miroestrol is biosynthesized in Pueraria mirifica, it can only be extracted in trace amounts. By chemically synthesizing the compound, larger quantities are able to be obtained and used. This study aimed to chemically synthesize miroestrol through a proposed synthesis pathway, by first synthesizing an intermediate in the reaction. A proposed mechanism for the synthesis of the intermediate, 5-(7-hydroxy-2H-chromen-3-yl)benzene-1,2,4-triol, was tested, and will be used for the synthesis of miroestrol once the expected product is obtained. The first two reactions in the intermediate synthesis were esterification and acylation. After refluxing, washing, separation using column chromatography, and NMR spectrometry, multiple trials showed that the esterification reaction was successful in producing the expected product. The acylation included reacting the chemicals over an ice bath for two hours, then washing and separation by column chromatography. When the product from the acylation was put through the NMR spectrometry, there was a discrepancy in the results. After multiple trials of the esterification and acylation reactions, it was concluded that the procedure for esterification was successful, while the procedure for the acylation must be retested to ensure that the correct product is continuously obtained before moving forward with the intermediate synthesis.
Funder Acknowledgement(s): This research project was funded, in part, by a grant from the National Science Foundation awarded to Lorraine Fleming, Wayne Patterson, and Mohamed Chouikha, principal and co-principal investigators of GEARUP.
Faculty Advisor: Kamla Deonauth, firstname.lastname@example.org
Role: As this research project is still in the preliminary stages, I did work that is critical to the synthesis of the miroestrol compound. Before the synthesis for miroestrol could even begin, an intermediate in the mechanism had to first be synthesized. My research mentor proposed a synthesis pathway for the intermediate synthesis. Throughout the summer, I worked on the first two reactions in his proposed mechanism. The first two reactions were esterification and acylation. During my time, I perfected the esterification reaction and continuously got the product we were looking for. The acylation reaction produced different results each time, suggesting that we needed to try a new procedure to ensure that we were getting the correct product in order to move on to the next reaction.